132785-33-2

Basic information

• Product Name: 4-(2-methoxyphenyl)-2-carboxy-3-pyrrolidineacetic acid
• Synonyms: 4-(2-methoxyphenyl)-2-carboxy-3-pyrrolidineacetic acid;(2S,3S,4S)-3-(carboxymethyl)-4-(2-methoxyphenyl)pyrrolidine-2-carboxylic acid
• CAS NO: 132785-33-2
• Molecular Formula: C₁₄H₁₇NO₅
• Molecular Weight: 0
• Mol File: 132785-33-2.mol

Chemical Properties

• Boiling Point: 524.7°Cat760mmHg
• Flash Point: 271.1°C
• Appearance: /
• Density: 1.284g/cm³
• Vapor Pressure: 7.78E-12mmHg at 25°C
• Refractive Index: 1.556
• CAS DataBase Reference: 4-(2-methoxyphenyl)-2-carboxy-3-pyrrolidineacetic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(2-methoxyphenyl)-2-carboxy-3-pyrrolidineacetic acid(132785-33-2)
• EPA Substance Registry System: 4-(2-methoxyphenyl)-2-carboxy-3-pyrrolidineacetic acid(132785-33-2)

Safety Data

• Hazardous Substances Data: 132785-33-2(Hazardous Substances Data)

Usage

InChI:InChI=1/C14H17NO5/c1-20-11-5-3-2-4-8(11)10-7-15-13(14(18)19)9(10)6-12(16)17/h2-5,9-10,13,15H,6-7H2,1H3,(H,16,17)(H,18,19)/t9-,10+,13-/m0/s1

Upstream product

• 89813-47-8 N-(tert-butoxycarbonyl)-(2S,4R)-4-hydroxyproline benzyl ester 
• 51-35-4 4R-4-hydroxyproline 
• 1218815-80-5 2-[(2S,3S,4S)-1,2-di-(tert-butoxycarbonyl)-4-(2-methoxyphenyl)pyrrolidin-3-yl]acetic acid 
• 1630067-73-0 (R,E)-6-(benzyloxy)-1-(methoxymethoxy)hex-3-en-2-yl 2-(2-methoxyphenyl)acetate 
• 1630067-74-1 (2S,3R,E)-3-[2-(benzyloxy)ethyl]-6-(methoxymethoxy)-2-(2-methoxyphenyl)hex-4-enoic acid 
• 93-25-4 2-methoxyphenylacetic acid 
• 7417-18-7 2-methoxyphenethyl alcohol 
• 126891-21-2 (2S,3S,4S)-3-Methoxycarbonylmethyl-4-(2-methoxy-phenyl)-pyrrolidine-2-carboxylic acid methyl ester 
• 1630067-76-3 C₂₄H₃₃NO₄ 
• 1630067-58-1 (R,E)-6-(benzyloxy)-1-(methoxymethoxy)hex-3-en-2-ol 
• 1630067-81-0 methyl (2S,3S,4S)-3-(2-hydroxyethyl)-2-(hydroxymethyl)-4-(2-methoxyphenyl)pyrrolidine-1-carboxylate 
• 1630067-80-9 methyl (2S,3S,4S)-3-[2-(benzyloxy)ethyl]-2-(hydroxymethyl)-4-(2-methoxyphenyl)pyrrolidine-1-carboxylate 
• 1630067-79-6 methyl (2R,3S,4S)-3-[2-(benzyloxy)ethyl]-4-(2-methoxyphenyl)-2-vinylpyrrolidine-1-carboxylate 
• 1630067-78-5 methyl {(2S,3R,E)-3-[2-(benzyloxy)ethyl]-6-hydroxy-2-(2-methoxyphenyl)hex-4-en-1-yl}carbamate 

Relevant articles and documents

A unified strategy for kainoid synthesis

A unified strategy for kainoid synthesis was developed. The key features of the strategy involve a Claisen-Ireland rearrangement to construct the contiguous stereogenic centers and a palladium-catalyzed formation of the pyrrolidine ring with complete stereoselectivity. The present protocol has enabled rapid access to a wide range of kainoids with diverse types of substituents (alkenyl, aryl, and alkyl groups) at the 4-position of the pyrrolidine ring, starting from the common intermediate and appropriate acetic acid derivatives. To test the generality of the strategy, we have accomplished the syntheses of kainic acid, o-methoxyphenyl derivative (MFPA), and a novel cyclopropyl derivative (CPKA), using 3-methylbut-3-enoic acid, 2-(2-methoxyphenyl)acetic acid, and 2-cyclopropylacetic acid, respectively.

Practical synthesis of Kainoids: A new chemical probe precursor and a fluorescent probe

A practical total synthesis of kainoid MFPA (5) was achieved in only six steps, via a novel Ni-catalyst-mediated asymmetric conjugate addition reaction. Furthermore, a fluorescein-based fluorescent ionotropic glutamate receptor probe 28 was efficiently sy

Diastereo- And enantioselective conjugate addition of α-ketoesters to nitroalkenes catalyzed by a chiral Ni(OAc)2 complex under mild conditions

(Figure Presented) A highly efficient, catalytic, dlastereo- and enantloselectlve conjugate addition of a-ketoesters to nltroalkenes has been devised. The reaction was applicable to various substrates. Notably, the combination of endogenous and exogenous bases was effective, allowing a small amount of the catalyst (0.1 -1 mol % NI) to promote the reaction efficiently. The synthetic utility of this reaction was demonstrated In the synthesis of substituted pyrrolidine derivatives, whose stereochemistry Is closely related to biologically Important natural products such as kainic add. Copyright

A new synthetic method for an acromelic acid analog, a potent neuroexcitatory kainoid amino acid, via photoinduced benzyl radical cyclization

A new synthetic method for an acromelic acid analog, MFPA, was developed. The key step is the photoinduced benzyl radical cyclization with excellent stereoselectivity.

Towards a versatile synthesis of kainoids II: Two methods for establishment of C-4 stereochemistry

Benzylic lactone hydrogenolysis and enamide reduction were used to generate protected C-4 aryl substituted kainoid analogues which were deprotected to their corresponding free amino acids. X-ray crystographic data were obtained for the C-4 2-MeOPh- analogue.

Synthesis of new acromelic acid congeners: Novel neuroexcitatory amino acids acting on glutamate receptor

A general synthetic method of acromelic acid congeners was developed. Various C4-substituents of this family was introduced by the substitution reaction of the corresponding tosylate with diaryl copper lithium. Phenyl derivative 11 showed comparable excitatory activity with kainic acid, and o-anisyl derivative 12 had most potent activity in this family.

Simple analogs of acromelic acid, which are highly active agonists of kainate type neuroexcitant

The highly stereoselective synthesis of acromelic acid analogs; 3a and 3b, was achieved. The new kainoid 3b was found to be the strongest neuroexcitant among the kainoids known so far.